Sequential Copper(I)‐Catalyzed Reaction of Amines with <i>o</i>‐Acetylenyl‐Substituted Phenyldiazoacetates

Peng, Cheng; Cheng, Jiajia; Wang, Jianbo

doi:10.1002/adsc.200800249

Cited by 37 publications

(18 citation statements)

References 56 publications

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“…Wang and co-workers have developed this idea very successfully for the combination of C−N bond formation via catalytic N−H insertion and catalytic alkyne hydroamination using a single copper-based catalyst. 464 A phenyldiazoacetate analogue bearing an o-alkynyl group was chosen as a suitable substrate. In the event, the (oalkynylphenyl)diazoacetate 134 was subjected to tetrakis-(acetonitrile)copper(I) hexafluorophosphate in the presence of aniline to yield isoindole 135 in 90% yield (Scheme 170).…”

Section: X−h Insertion Reactions Of Diazocarbonyl Compoundsmentioning

confidence: 99%

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Ford¹,

Miel

Ring³

et al. 2015

Chem. Rev.

1,341

585

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Section: X−h Insertion Reactions Of Diazocarbonyl Compoundsmentioning

confidence: 99%

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Ford¹,

Miel

Ring³

et al. 2015

Chem. Rev.

1,341

585

View full text Add to dashboard Cite

“…[43] Wang et al reported the Cu-catalyzed domino NÀH insertion-intramolecular hydroamination for the synthesis of isoindoles (Scheme 26). [44] The first step is the insertion of a carbenoid, generated from a-diazoester 75, into the NÀH bond of arylamine 76. After the formation of intermediary phenylglycine derivative 77, intramolecular hydroamination occurs to give isoindole 78.…”

Section: Domino Transition Metal-acid-catalyzed Reactions In Auto-tanmentioning

confidence: 99%

Auto‐Tandem Catalysis: A Single Catalyst Activating Mechanistically Distinct Reactions in a Single Reactor

Shindo

Takemoto

Takasu

2009

Chemistry A European J

256

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Domino reactions have received great attention as efficient synthetic methodologies for the construction of structurally complex molecules from simple materials in a single operation. Catalysts in domino reactions have also been well studied. In these reactions, a catalyst activates the substrate(s) only once, and the structure of the product is delineated at that time. Recently, the new concept of "tandem catalysis" in domino reactions, in which catalyst(s) sequentially activate more than two mechanistically distinct reactions, has been proposed. Tandem catalysis is categorized into three subclasses: orthogonal-, auto-, and assisted-tandem catalyses. Auto-tandem catalysis is defined as a process in which one catalyst promotes more than two fundamentally different reactions in a single reactor. An overview of recent and significant achievements in auto-tandem catalysis is presented in this paper.

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“…Wang et al. reported the Cu‐catalyzed domino NH insertion–intramolecular hydroamination for the synthesis of isoindoles (Scheme ) 44. The first step is the insertion of a carbenoid, generated from α‐diazoester 75 , into the NH bond of arylamine 76 .…”

Section: Domino Transition Metal–acid‐catalyzed Reactions In Auto‐tanmentioning

confidence: 99%

Glyco‐pseudopolyrotaxanes: Carbohydrate Wheels Threaded on a Polymer String and Their Inhibition of Bacterial Adhesion

Kim

Ahn

Park

et al. 2010

Chemistry A European J

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We report glyco-pseudopolyrotaxanes composed of cucurbit[6]uril-based mannose wheels (ManCB[6]) threaded on polyviologen (PV), which not only effectively induce bacterial aggregation, but also exhibit high inhibitory activity against bacterial binding to host cells. Three glyco-pseudopolyrotaxanes (1-3), which have 10, 5, and 3 ManCB[6] wheels, respectively, on a PV string, were prepared and characterized. Bacterial aggregation assays and hemagglutination inhibition assays illustrated the specific and multivalent interaction between the glyco-pseudopolyrotaxanes and E. coli ORN178. Compound 3 was especially effective at inducing bacterial aggregation and showed 300 times higher inhibitory potency than monomeric methyl-α-mannoside (Me-αMan) for ORN178-induced hemagglutination. Furthermore, we demonstrated their inhibitory activities for the adhesion of ORN178 bacteria to urinary epithelial cells as a model of urinary tract infection. Our findings suggest that these supramolecular carbohydrate clusters are potentially useful in antiadhesion therapy.

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Sequential Copper(I)‐Catalyzed Reaction of Amines with o‐Acetylenyl‐Substituted Phenyldiazoacetates

Abstract: A highly efficient, tetrakis(acetonitrile)- 4 PF 6 ]-catalyzed tandem Cu(I)-carbene N À H insertion/ Cu(I)-catalyzed hydroamination of alkynes, which leads to sequential formation of two C À N bonds to yield isoindole derivatives, has been developed.

Cited by 37 publications

References 56 publications

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Auto‐Tandem Catalysis: A Single Catalyst Activating Mechanistically Distinct Reactions in a Single Reactor

Glyco‐pseudopolyrotaxanes: Carbohydrate Wheels Threaded on a Polymer String and Their Inhibition of Bacterial Adhesion

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